The Cowboys are a perennial power in the Berkshire League in multiple sports. Litchfield proper hosts the Litchfield Hill Road Race on the second Sunday in June. The event draws runners from around the world.
The Golden Bears are a Berkshire League force, having put together a string of State Championships that would compare to any in the state. Girls Basketball and Field Hockey titles have become the norm in this classic town.
The Raiders belong to the Naugatuck Valley League and play their home games in the Connie Donahue Gymnasium, their football and soccer games in the Robert H Frost Complex, and their baseball games at historic Fuessenich Park.
Two schools, Northwestern and Gilbert, make for great rivalries in this northernmost Berkshire League town. The Yellowjackets (Gilbert) and the Highlanders (NW) combine under one helmet in football and call themselves “GN” on the gridiron.